


A Comedy of Fucking Errors

by GythaOgg



Category: Supernatural
Genre: Accidents, Awkward Sexual Situations, Best Friends, Castiel/Dean Winchester First Time, Castiel/Dean Winchester Mutual Pining, Destiel - Freeform, First Time, Friends to Lovers, M/M, Pining
Language: English
Status: Completed
Published: 2019-08-21
Updated: 2019-08-21
Packaged: 2020-09-23 11:43:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,549
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20339572
Author URL: https://archiveofourown.org/users/GythaOgg/pseuds/GythaOgg
Summary: Ever had Murphy's law sex? Not BAD sex, but a sexual encounter / disaster, full of accidents, embarrassments, or minor injuries? Sex where you damn well better have a good sense of humor, if you're ever going to see each other again?Dean and Castiel have been friends for 8 years, and have been pining for each other (in secret) for most of that time. Now they're both single, and their feelings are out in the open. They're a couple, but they've been taking it slow, and now they're FINALLY going to have sex! Enter Murphy's law: everything that can go wrong, will go wrong.





	A Comedy of Fucking Errors

Today is a big day; a day nearly a decade in the making.

Dean Winchester and Castiel Novak have been friends for ages. They met as college freshmen, were roommates for the last two years of college, and for three years after, until Castiel got engaged and moved in with Daphne, more than a year ago. All that time, Dean and Cas have remained best friends, and all that time, Dean has been secretly in love with him. For the first few years, he was in denial, trying to convince himself he was straight. By the time they graduated from college, he was out of the closet as Bi, but still trying to work up the courage to tell Cas how he felt. By the time they were 24, Castiel was dating Daphne. Dean, being a gentleman, refused to disrespect anyone's relationship, so he resigned himself to wait for the happy couple to break up. By 26, however, Cas and Daphne were engaged, and Dean knew he had missed his best chance at happiness. He helped his best friend pack up and move, and though they still saw each other often, Dean felt like he had lost his soul mate.

As Fate would have it, Cas had been pining for Dean since they were 19, but had no idea that Dean felt the same. Castiel was never very good at flirting, but he tried. He stared at Dean so much that it became a running joke among their friends. He made Dean coffee in the morning and brought him pie at work. He rubbed his shoulders when Dean had a long day and listened to every story about his Engineering projects. Unfortunately, the parade of one night stands that Dean brought home, convinced Cas that he was simply not interested in being anything more than friends. So eventually, Cas started saying 'yes' when men and women asked him out, and soon he started seeing Daphne. She was sweet, smart, patient, pretty, and had a great sense of humor. She and Castiel got along remarkably well and had a lot in common. The only real drawback was that Dean didn’t like her. He was polite, of course, but he never really warmed up to her. 

When he and Daphne had been together for about a year and a half, their friends and families started asking if there was a wedding in their future. They both laughed off the suggestions, but he could tell Daphne liked the idea. A few months later, Castiel decided to propose. His feelings for Dean hadn’t dimmed in the slightest, and it was agonizing to watch him bring home random men and women. In fact, it seemed like Dean brought even MORE people home, once Daphne had come into the picture. Cas knew he needed to get out of their apartment and move on with his life, or he would never get over Dean. No, he wasn’t truly in love with Daphne, but she was a wonderful person and a great friend, and Castiel was sure she would make a good wife.

Unfortunately, Daphne was no fool. Castiel was a great boyfriend. He was kind, gorgeous, considerate, strong, and intelligent. She knew all along that Cas and Dean were much closer than typical friends, even best friends, but she loved Cas, and she trusted him to be honest with her. Within a year, however, it was obvious that the less time Cas spent with Dean, the less happy he was, and Daphne realized that Cas wasn’t lying to her, he was lying to himself. She sat Cas down and told him that he shouldn't settle for something that wouldn’t make him happy, and that he needed to be honest with himself. She deserved a husband who looked at her the way Cas looked at Dean, and Dean deserved to know the truth. Cas cried, Daphne cried, and they talked all night about truth, love, and fear. In the end, Daphne moved out, but they remained friends. When Dean texted Cas a few days later, he explained that he and Daphne had split up. Within 30 minutes, Dean was on Cas’s doorstep with beer, pizza, and ice cream, and Cas told him exactly why Daphne had left.

Dean, of course, confessed his feelings as well. There was a lot of relief, a little awkwardness, and a surprising amount of money changing hands among their friends. Of course, since life is not a romance novel, and Cas had just gotten out of a serious relationship, he and Dean decided to take things slow. They spent more time together, they held hands, they went on dates, they kissed. What they did NOT do, was have sex, or even sleep in the same bed, in the beginning. Not even blow jobs! That was a month ago.

Yesterday, Cas decided that he was ready. Now, he and Dean have plans to spend the whole weekend locked in Castiel’s house, 'making up for lost time'. So, today is a big day. 

Things do not go as planned.

Dean arrives at Cas’s door at 7pm on Friday, with 2 six-packs of Sam Adams, a bag of takeout from the Chinese place down the street, and a bad case of the jitters. When Castiel answers the door, he finds Dean biting his lip and fidgeting, shifting from one foot to the other. “You OK?” he asks Dean, grinning. Dean blushes and looks to the left, then up, before finally meeting his eyes.

“Is it weird that I’m nervous? I mean, we’ve known each other forever, and it’s not like I'm a virgin, over here. Why am I nervous?”

Cas laughs and pulls Dean into the house. “It’s not weird. There’s a lot of . . . anticipation going on, I think. From both sides.” Cas answers, taking the bag of takeout and kissing Dean on the cheek.

They eat and have a couple of beers, and by the time they’re putting their dishes in the sink, they’re both much more relaxed. As Cas turns away from the kitchen counter, Dean catches his hand and pulls him close. Cas reaches up and runs a hand through Dean’s hair, staring into his bright green eyes. No longer nervous, Dean smirks and licks his lips, leaning in slightly. Cas follows the motion of his tongue, and leans in as well, not noticing that Dean was suddenly much closer than he’d been a moment ago.

***BONK***

Both men wince and pull back, rubbing their foreheads. “Oooh. Shit! Sorry, sorry!” Dean mumbles, blinking. Cas apologizes as well, chuckling.

“Can we try that again?” he asks. Dean hums, and takes Cas’s face in both hands, telegraphing his motions with great exaggeration. Cas laughs at him, as their lips meet (this time with no headbutting), and they share a long, sweet, easy kiss.

The kissing quickly gets more heated, however, and soon, Cas grabs Dean’s thighs and hoists him up onto the island. “Hey! That’s . . . wow. OK.” Dean babbles, flushing deep red. He’s clearly flustered by being manhandled, but his pupils are blown wide, and he’s panting a little.

Now it’s Cas who’s smirking. He steps forward, pressing between Dean’s legs, and slips his hand up, under Dean’s t-shirt, kissing his neck. “Is this OK?” he asks, quietly. Dean’s reply is something between a hum and a moan, but he nods, wrapping his arms around Castiel’s shoulders and tangling one hand in his dark, fluffy hair.

Within a few minutes, Dean’s shirt is around his neck, and Cas leans back to pull it over his head, thoroughly mussing up his carefully styled hair. Cas dives back in quickly, nipping at Dean’s collar bone, and kissing his way down his chest, to lick at his nipples. Dean gasps, digging his short nails into Cas’s shoulder. Pressed tight against him, Cas can feel Dean growing steadily harder in his jeans, as he sucks and bites at his nipples. Dean presses his face into Castiel’s neck, licking and kissing everywhere he can reach, and pulling at the hem of Cas’s shirt.

“Off, off! Take this damn thing . . . “, he grunts, yanking the shirt up to Cas’s armpits. Cas pulls away long enough for Dean to yank the shirt up over his face, and Cas turns his head back and forth blindly, as it gets caught at a bad angle. In the struggle to get the offending piece of clothing off, Dean yanks up, just as Cas turns his face sharply to the left.

***CRACK***

“Owwwww! Shitshitshitowww!” howls Dean, cupping his right elbow. He cracks one eye open to see Castiel cradling his jaw, shirt crumped in one hand, looking stunned.

“Are you OK?” Cas asks, looking pointedly at Dean’s elbow. Dean winces again, feeling guilty.

“I’m fine, babe. Just, funny bone, ya know? Are you OK?” Cas nods, gingerly poking his jaw with one finger.

“Yeah, I’m alright. Might have a bruise tomorrow, though.” Dean’s eyebrows raise, in a poor imitation of his little brother’s famous puppy-dog expression.

“I’m sorry, babe. I swear I’m not this clumsy,” he whines. Cas squints, giving his boyfriend an assessing look.

“Maybe we should take this to the bedroom. Pillows, soft mattress. Safer environment.” Dean sees the sparkle in Cas’s eyes, and nods as seriously as he can manage.

“I think that’s for the best. Safety first,” he replies. Castiel’s expression is slowly becoming a sly grin, and he reaches for Dean’s hand, pulling his off the island.

The men hurry down the hall to the stairs, then up to the master bedroom. By the time they get to the bedroom door, they’re wrapped up in each other again, staggering down the hallway and pressing one another up against the wall, kissing and groping, gasping and groaning. They stumble towards the bed, toeing off shoes and socks. Dean can’t seem to manage Cas’s belt buckle, so he drops onto the bed to shuck off his jeans, and Cas steps back to battle his belt buckle alone.

Belt off, he stares at Dean, now naked on the bed, and shimmies out of his own pants. Mesmerized at the sight of him, Cas takes a step forward, but suddenly finds himself on the floor, in a tangle of skinny jeans. Dean sits up on the bed and gapes at Castiel, sprawled on the soft grey rug. He’s silent for a long moment, then snorts, covering his mouth. The snort becomes a chortle, then a sort of choking giggle. Cas glares up at him, but can’t help but chuckle, too. As he tugs at the jeans still wrapped maliciously around his ankle, he hears Dean flop back onto the bed again, cackling like a hyena. Cas climbs up on the bed, finally nude, and brackets Dean with his arms.

“Oh, come on. You know that was sexy. Admit it!”

Dean’s laughter finally peters out, and he stares up at Cas fondly, wiping his eyes. “Ohhh, super sexy. Hottest thing I ever saw. Do it again!” he wheezes. Cas growls in response, leaning down to suck one nipple into his mouth, turning Dean’s wheeze into a gasp.

“Mmm,” he mumbles, “do THAT again!” So Cas does. Then he kisses his way down Dean’s flat stomach, running his tongue along the lines of his abs, over his hip bones, and sucking little marks into the soft skin just below his hips. By the time he gets to Dean’s cock, Dean is a squirmy wreck, whimpering and hissing at Cas to “come on . . . oh fuck, please . . . put your mouth on me, Cas”. Castiel is, of course, happy to oblige.

After a few minutes of rather enthusiastic cocksucking, Cas’s hand starts to wander further south. He strokes across Dean’s hole, circling it slowly, and soon enough, Dean is pressing against his hand, trying to grind against his finger. Cas pulls off with a wet ‘pop’ and stares up at his boyfriend, making a show of putting two fingers in his mouth and getting them sopping wet. Then, he’s back to work, mouthing at Dean’s balls, as he slowly presses one fingertip inside Dean. Dean whines and tries to push down, eager to take more, but Cas is careful, gentle. He twists his hand, pressing one finger in slow, petting Dean from the inside. He takes Dean’s balls into his mouth and sucks gently, pumping his finger in and out, making Dean moan and twist his hips, impatiently. After a few seconds, he moves his mouth to Dean’s perineum, as he inserts the tip of a second finger, but only for a moment. Cas pulls back, prompting an indignant squeak from Dean, and leans to one side of the bed, winking. He opens the top drawer of the nightstand, and freezes.

Dean gives him a few seconds before asking, “Cas?”, and is rewarded with a scowl from his boyfriend. Castiel turns back to the bed with a bottle of lube . . . a mostly empty bottle of lube.

He tilts his head to peer closer at the bottle, and mumbles, “it leaked”. Now that Dean is looking, he can see goop down one side of the cap, dripping off the plastic. There is not a lot of lube left inside. 

“Fuck it, there’s enough for right now. We’ll go out in the morning and get more,” Dean huffs, pulling at Cas’s hips. Castiel makes another lunge and comes back with a strip of condoms. He hastily finishes prepping Dean, then slides back up his body to kiss him, long and slow. Dean smiles into the kiss, and weaves his fingers into Cas’s hair, dragging his head back far enough to make eye contact. “Cas, baby?” he purrs, still smiling. “Quit fooling around and put your cock in me. Right. Now!”

Cas grins menacingly at him. “As you wish,” he whispers.

Cas sits up and tears open one of the condom packets, staring at Dean like he’s a gourmet meal. He pulls the condom out and looks down, to put it on. “Oh, for fuck’s sake!” he wails. Confused, Dean glances down to Cas’s cock. It’s still huge and hard, flushed dark red, and gorgeous . . . so what’s the problem? Then Castiel holds the condom up for Dean to see. It’s torn. “I think I tore it when I ripped open the foil” Cas mutters. Then, cheeks flushing from embarrassment, “It’s kinda been awhile”.

With barely a pause, Dean sits up and snatches the condom out of Castiel’s hand, tossing it to the floor. He glances down to the bed, where three more condoms are laying there, next to the sticky bottle of lube. Grabbing one, he (cautiously) rips it open, winking up at Cas, and leans forward.

“Allow me,” he rumbles, kissing the head of Cas’s dripping cock, before rolling the condom on. Dean drizzles what’s left of the lube into his hand, coating Cas with it, then lays back, knees bent, to stroke his own dick. “Now then . . . where were we?” he asks, pursing his lush, pink lips.

Cas growls, and hooks his hands under Dean’s knees, dragging him closer. He runs one finger down the inside of one thigh, making Dean shiver, then grabs a pillow ad slips it under Dean’s ass. He lines himself up and presses the head of his cock against Dean’s entrance, slowly pushing in. He tries to maintain eye contact with Dean, but he can’t help staring down, watching himself sink into the love of his life. All these years, Cas never thought he stood a chance with Dean. Never had the courage to tell him how he felt. And now, this was finally, finally happening.

When he is pressed flush against Dean’s body, Cas lets out a breath he didn’t know he was holding. He opens his eyes (_wait, when did he close his eyes?_) at Dean’s hummed “mmmm”, and sees Dean staring up at him with a lazy smile and a dazed, hungry look in his eyes. He holds still, letting Dean get used to his size, but not for long. Almost immediately, Dean starts to roll his hips, biting his bottom lip. “Fuck me, Cas.”

That’s all that Cas needs to hear. He pulls back halfway and slides in hard, jolting Dean up the bed a couple of inches, and making him grunt. He pulls back further, and starts up a pounding rhythm, with Dean grinning and moaning his approval, wrapping his legs around Cas’s waist. Soon there’s sweat dripping from both men, and Cas grabs Dean’s long legs and folds them up, Dean’s knees against his chest. He uses the leverage of Dean’s thighs to pull him into every thrust, reveling in the gasps and curses coming from Dean’s mouth. This is better than any sex he’s ever had before, and Cas knows why. He slows down a bit, leans forward and finds Dean’s hand, threading their fingers together and looking deep into those beautiful green eyes. Dean’s eyelashes are wet, and he has the most beautiful, gentle smile on his face. He leans up, squeezing Cas’s hand, and their lips meet in a desperately sweet kiss.

All at once, the mood shifts, and Cas feels Dean’s legs drop down, one arm wraps around his back, and then Dean is rolling them over in one swift, smooth motion. It happens so fast that Cas is honestly a little stunned to suddenly find himself on his back, with a rather smug-looking Dean straddling him. He opens his mouth to say something, but shuts it with a moan, as Dean pushes himself up on his knees and drops down hard, impaling himself on Cas’s dick. Dean shuffles forward a bit, changing the angle, and begins bouncing enthusiastically, grunts becoming shouts as Cas hits his prostate again and again. Dean’s hand wraps around his own cock as he throws his head back. Thoroughly enjoying the view, Cas grabs Dean’s hips and braces his feet flat on the bed, thrusting up to meet Dean’s body. Dean’s eyes fly open, and he braces one arm on Cas’s chest, staring wide-eyed, his mouth agape. After a while, Dean abruptly drops down and swivels his hips, grinding on Cas’s cock. His brows furrow, his nostrils flare, and his jaw clenches, growling out Cas’s name. Dean’s ass squeezes Cas tight as he comes, pushing Cas right over the edge with him. Castiel’s hands tighten on Dean’s hips, hard enough to bruise, but when Dean collapses on top of him, panting, Cas wraps his arms around him and holds him like he’s the most precious thing ever made.

A few minutes pass, and Cas kisses the top of Dean’s head. “You’re amazing,” he whispers. “And really fucking heavy. You’re squishing me.” Dean laughs against Castiel’s neck and rolls carefully off him. Cas tosses the condom into the trash can a few feet away, then sits up, turning to face Dean, and strokes one hand down his flank. “You’re beautiful, you know that? Not just hot. You’re absolutely beautiful, inside and out. I’ve always wanted to tell you that.”

Dean blinks up at him, then blushes and shakes his head, looking down and fiddling with the comforter. “Jeez, Cas,” he mumbles, with a shy grin. Then, he lifts his chin, hesitates just a moment, and looks Cas resolutely in the eye. “So are you, Cas,” he says quietly. “I love you.”

Cas loses his breath for a second. This is the first time Dean has ever explicitly said those words to him. He knew it already, of course; they’d discussed their feelings many times in the last few weeks, but Dean’s always struggled to say those particular words, even with his family. Cas’s heartbeat thuds in his ear, and he takes a deep breath, smiling so wide his cheeks ache. “I love you too, Dean. Always have, and I always will,” he says. He leans forward and brings Dean’s hand up, kissing the knuckles.

They stare at each other for a while, grinning like idiots, before Dean mumbles, “we should get cleaned up”. Cas nods, and swings his legs around to get off the bed. Apparently, Dean has the same idea, and sits up at exactly the same time.

There’s a loud ***SMACK*** as Cas’s foot connects with Dean’s cheek. It’s not hard enough to halt Dean’s forward momentum, however, which tilts Cas off balance, tipping him right off the bed. Cas sprawls flat on his back, staring up at the ceiling, as Dean scrambles to the edge of the bed and leans over to check on him. “Jesus, Cas – are you alright?”

“What the fuck is happening today?” Cas asks in reply, throwing up his hands and giggling, helplessly.

Dean starts laughing as well, and slides down to lie on the floor, resting his head on Cas’s chest. “I don’t know, babe. At least the sex was good!”

Cas drapes an arm around Dean. “Yes, yes it was.”

There’s a long pause, but Dean finally moves. “OK, I’m gonna get up, and very carefully walk to the bathroom. Alone. You’re gonna stay right here on the floor, where it’s safe. No more accidents, K?”

Cas smiles softly and nods. “K.”

It’s not until Dean stands up and takes his first step, that Cas remembers the leaky bottle of lube that had fallen off the bed with him. “Shit! Dean, wait . . . “ 

***CRASH***


End file.
